


Detention With Mr Novak

by 5t0rmtr00p3r



Category: Supernatural
Genre: Alternate Universe - High School, Anal Sex, BDSM, Blackmail, Butt Plugs, Cock & Ball Torture, Detention, Dildos, Dom!Cas, Dom/sub, Filming, Forced Crossdressing, Gags, Hand Jobs, Humiliation, M/M, Nipple Clamps, Nipple Licking, Nipple Play, Plot What Plot/Porn Without Plot, Student Dean, Sub!Dean, Teacher Castiel, Teacher-Student Relationship, Video Cameras
Language: English
Status: Completed
Published: 2015-03-16
Updated: 2015-03-16
Packaged: 2018-03-18 04:07:10
Rating: Explicit
Warnings: Rape/Non-Con
Chapters: 1
Words: 2,525
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/3555452
Author URL: https://archiveofourown.org/users/5t0rmtr00p3r/pseuds/5t0rmtr00p3r
Summary: <blockquote class="userstuff">
              <p>Dean has been given detention hundreds of times, but never by Mr Novak.  He's about to find out why Mr Novak's classes are always very well behaved...</p>
            </blockquote>





	Detention With Mr Novak

Dean paced outside Mr Novak's classroom. He'd been given detention hundreds of times, but never by Mr Novak. And the quiet hush that had fallen over the room when Mr Novak had told him to stay behind after school had sent chills down his spine. Swallowing his discomfort, because no detention could be _that_ bad, he knocked on the door.

Instead of hearing Mr Novak's voice telling him to come in, footsteps made their way to the door and it opened a crack to reveal his bright blue eyes staring out at him.

"Ah, Dean," he said, swinging the door open wider. "Come in."

Hesitantly walked in, his eyes immediately drawn to the video camera set up in front of the whiteboard. When he heard the door close and lock behind him, he swung round to face his teacher. This was all levels of wrong.

"Take the clothes from my desk and go into the cupboard to get changed while I finish setting up."

Dean dropped his bag onto a desk and went to look at the clothes. He held up the skirt. "These are girls' clothes," he observed.

"Yes," Mr Novak replied.

When he realised that his teacher wasn't going to say anything else, he picked up the clothes and went to get changed. But Mr Novak stopped him when he re-emerged. "You aren't wearing the bra."

"No."

"Why not?"

"Because I'm not a girl."

"Dean, you begged me not to call your parents and bring them down to the school to discuss your behaviour. Have you changed your mind?"

"No, but—"

Castiel picked up his phone. "Every time you hesitate or refuse to obey, I will enter another digit of your parents' number until it's ready to dial. I have entered the first number."

Dean flushed and turned back to the cupboard.

"Wait."

He turned back.

"Are you wearing the panties?"

"Yes."

Castiel cocked an eyebrow. "Really? Let me see."

"No."

Castiel's finger hovered threateningly over the keypad of the phone, so Dean reluctantly raised the skirt to expose his bare genitals, no panties in sight.

"You lied to me."

"Sorry. I'll go put both on."

"No."

Dean looked confused.

"You look better without them. But put the bra on."

A moment later Dean came out again, this time the lacy pink bra could be seen under the white shirt.

"Unbutton your blouse... that's it... not too much, just so that we can see the top of your bra. Perfect. Now the first part of your detention will be to write fifty lines on the board; 'Only bad boys get their teacher hard in class.'"

"Did I get you hard?" Dean asked cockily, before remembering what he was wearing and deciding it wasn't the best idea.

"See for yourself," Castiel said, exposing himself.

Dean swallowed dryly. Castiel's long, thick cock jutted proudly out of his pants, pearly drops of precome gathered at the head.

"And you are a very, _very_ bad boy. Now, about those lines..."

Dean picked up the pen, aware of the _beep_ indicating that Castiel had started filming.

"And for the duration of your detention you will refer to me only as 'sir'."

"Yes, sir."

"Good. Begin."

Dean started writing, his normally bad writing worse on the board. But then so was everyone's.

_Only bad boys get their teacher hard in class._

Castiel's breathing was heavy behind him as he watched, distracting him to the point that he made mistakes.

_Only bad boys get teacher hard in class._

"Don't correct it – start a new line. Anything less than perfect doesn't count towards your fifty lines."

Gritting his teeth, he started over.

_Only bad boys get their teacher hard in class._

"Are you a bad boy, Dean?"

_Only bad boys get their teacher hard in class._

"Yes, sir."

_Only bad boys get their teacher hard in class._

"Then I suppose you'll have to be punished. Do you agree?"

_Only bad boys get their teacher hard in class._

Dean could feel the back of his neck growing warm. "Yes, sir."

_Only bad boys get their teacher hard in class._

"Good."

_Only bad boys get their teacher hard in class._

As Dean neared the bottom of the board, he crouched down so it was easier to write.

"No, don't bend your knees – bend over."

Dean froze. If he bent over then his ass was going to be on camera.

"I've entered the next digit into my phone."

Dean straightened his legs and bent over, feeling a breeze from the open window blowing across his buttocks.

_Only bad boys get their teacher hard in class._

"Good boy."

_Only bad boys get their teacher hard in class._

"Nearly there."

_Only bad boys get their teacher hard in class._

Dean put the pen down when he was finished.

"Very good. Now do you think you've learned your lesson?"

"Yes, sir."

"Look at me, Dean."

Dean turned around.

"Look at my cock."

Dean reluctantly looked down at the thick red cock and the wet patch gathering on the thigh of Mr Novak's pants.

"Do you think you've learned your lesson?"

"Well to be fair, this isn't _class_ —"

"Don't cheek me, boy."

A tear slipped down his cheek and, afraid of what would come next, he choked out, "Sorry, sir. No, sir. I don't think I've learned my lesson."

"Perhaps you need something in your mouth to stop you from being so cheeky..."

Dean looked at his teacher's cock again, thinking that there was no way he could take it.

"No, not my _cock_ , Dean. Not yet, anyway..." he added. "This." He held up a spider gag, which he fastened round Dean's face so that his mouth was stretched uncomfortably wide. "Now stand in front of the camera."

Dean obeyed.

"Only bad boys get their teacher hard in class, but good boys get their teacher off when they accidentally do. Are you a good boy, Dean?"

"Yes, sir?" he struggled to say around the gag.

"No, I don't think you are. But I think that you want to be."

Dean nodded eagerly despite the tears in his eyes. Anything to make the humiliation end sooner.

"Strip for me. Slowly."

Clumsily Dean unfastened the buttons on the blouse, backwards from what he was used to.

"Now turn around, let it slide off your shoulders, and unhook your bra. Good... Turn round again. Rub your pretty little breasts through your bra. Squeeze your titties. Good, good... Let me see them."

Dean slid the bra off, exposing pink nipples hardened by his touch.

"You're so eager for it, aren't you?" Cas said, not wanting an answer. "Pinch your nipples. Pull them and twist them. Make them hurt."

He started crying openly as he followed his teacher's instructions, shame pooling in his gut.

"I'm not convinced they hurt, Dean. Make me believe you're hurting or I'll put a couple of clips on them."

Dean pulled his nipples further out, twisted them harder, bit down on them with his nails until they were red.

"Better, much better. Lift your skirt up, let me see the panties you aren't wearing."

Snot was dripping from his nose as he cried, and saliva was leaking from his mouth. He shook his head.

"That's a third number, Dean."

Dean shook his head again, desperate, eyes wide and pleading.

"And a fourth..."

Dean sobbed and lifted his skirt, revealing his hard cock. It wasn't as long or as thick as Castiel's, but it was still impressive for his age.

"Take the skirt off and stand at my desk. Lay your cock on it," he ordered quickly, clearly aroused and improvising now.

Dean obeyed as Castiel moved the camera to record the new angle, then handed Dean two bulldog clips. "Clip your nipples. Or do you want me to do it for you?"

Dean held them out to Cas, who fastened them gently to Dean's already aching nipples, "Seeing as you played with them so beautifully."

Castiel picked up a wooden ruler and rubbed it along Dean's cock.

"Let's see if it's the pain or the humiliation that turns you on, shall we?"

Dean shook his head as the ruler tapped his cock lightly, and he howled.

"Oh, hush. I hardly touched you."

Cas smacked him again, harder this time, and Dean moved away.

"That's a fifth number, Dean."

Reluctantly Dean rested his cock on the table again.

"Ask me to hit your cock."

"Please hit my cock," he struggled to say around the gag.

Castiel removed it.

"Please hit my cock," he repeated.

"I don't believe you want it."

"Please hit my cock."

"No."

"Please hit my cock?"

"Better."

Please sir, would you hit my cock?"

_Smack._

Dean howled.

"Again."

"Please sir," Dean choked, "would you hit my cock?"

_Smack._

"Please sir, would you hit my cock?"

_Smack._

Come spurted out of Dean's cock, streaking some of the papers on the desk.

Castiel moved behind him, bending him over roughly and fucking him unforgivingly with the ruler. Dean begged him to stop as each thrust hit his prostate, but Castiel continued until Dean was a sobbing limp mess and his spent cock hung limply between his legs.

"Spread your legs."

He kicked them apart when Dean was slow to comply, then brought the ruler up between them to smack his balls.

"No!" Dean howled. "Please, no! Not there!"

_Smack. Smack. Smack._

He continued until Dean's cock grew hard again. "Oh, yes," Cas said. "You like the pain. Take the clips off. No, don't open them – pull them."

Dean pulled one off and screamed as blood rushed back there, the pain making him feel like his nipple was on fire.

"And the other one."

"Please, sir, no. Please."

"I'm growing impatient with you, Dean. We have established that you enjoy pain – why deny yourself?"

Dean clenched his teeth and pulled.

"Good boy" Mr Novak praised him once it snapped off, lowering him back onto the desk. He took one reddened nub in his mouth, swirling his tongue around it and sucked on it until Dean was moaning in pleasure. He gave the other the same treatment as he slowly fisted Dean's cock in his hand, alternating between the two until the pain ebbed and he was coming again. "Now what do you say when I've been so nice as to let you come?"

"Thank you, sir?"

"Like you mean it."

"Thank you, sir."

"Are you grateful?"

"Yes, sir."

"Are you a good boy?"

Dean hesitated. His teacher's cock was still hard. "I want to be, sir."

"Then suck my cock."

Dean dropped to his knees and took the head in his mouth. The salty taste was unpleasant on his tongue. Experimentally he licked at it, then, emboldened by Castiel's moans, sucked. He inched further down until he felt like he would choke and pulled back, then tried again. And again. And again. He could only fit half of Castiel's cock comfortably in his mouth, but that didn't stop Castiel from fisting his hair and fucking his mouth when he wasn't getting what he wanted. Dean let his jaw hang open, trying to ignore his body's desperate need for oxygen. Just as he thought he was going to pass out Castiel came, warm come spilling down his throat, and he pulled out.

"I think it's going to be very hard for you to be a good boy," he smiled. "You are beautiful. Now go home. And I want a thousand words on my desk tomorrow about what you liked and didn't like about this experience, and don't lie. Oh," he added as an afterthought. "And keep the underwear. You can wear it to school tomorrow, because I'm giving you a second detention to prove to me that you've learned how to be a good boy."

* * *

The next day Dean came to Castiel's room after school. He was instructed to strip in front of his teacher to prove he'd worn the underwear. The wet stain made it clear that he'd enjoyed the experience very much. He had Dean bend over the desk to watch the video from the day before while Cas read his homework. Dean's essay made very interesting reading. He didn't like being recorded, or having his cock caned, but he did admit to enjoy being told what to do and having his nipples clamped - though he noted the pain of pulling them off was too much. He made no mention of the underwear, but the wet stain spoke for itself.

He finished reading before the video ended, so he gave Dean minimal prep before fucking slowly into him. Dean was still too tight to risk fucking him balls-deep, but it was enough to get him off.

"You're a good boy, Dean," he praised him once he'd zipped himself up again. "A very good boy. And if you can take the whole length of my cock up your ass by next Friday I'll be sure to tell your parents how good you are on parents' evening."

"Thank you, sir."

* * *

Dean bought lube on the way home, stretching his ass. He did the same when he woke up in the morning, and again in the toilets at lunch. By the end of the day he was loose enough that he could comfortably take another half inch of Mr Novak's cock.

Castiel presented him with a dildo, larger than Dean but smaller than Cas. "Your homework," was all he said.

"Yes, sir."

"On Monday I expect you to prove to me that you can take all of it, and that's the only prep you'll get before I fuck you again."

"Yes, sir."

* * *

He practiced all weekend, and on Monday he found himself on all fours on Castiel's desk while his teacher watched him fuck himself with the dildo he'd bought him until he slid it all the way in.

"Well done," Cas praised him, before manhandling him into position to be fucked.

"I want to be a good boy, sir. I'll do anything to be a good boy," Dean rambled as Castiel's cock nudged his prostate again and again and again.

"I believe you," Castiel panted, and when he came he presented Dean with a plug, larger than the dildo. "You'll come to me before class tomorrow and insert it under my supervision, then at the end of the day you'll remove it in front of me before I fuck you. You may not take it out in between times."

"What if I need to take a shit?" Dean asked bluntly.

"You can come to me at lunch and beg. I know how much you hate begging, but I enjoy seeing you beg and you could use the practice."

* * *

By Thursday Dean could take all of Castiel's cock, though the stretch hurt.

"You'll get used to it," Castiel promised.

"I will?"

"Yes. You have detention every night after school until the end of the year."

"But—"

"You have a fucking fantastic ass, Dean, and I'm not letting it go. I might even try to persuade your parents that you need extra tuition after school – at my house, of course. I have so many toys I want to try out on you."


End file.
